Microsoft Is Trying to Be Your Friend, and It May Actually Win You Over

Microsoft today is friendly and approachable. It’s peculiar and self-aware. It makes fun of itself. When Terry Myerson, an executive vice president in its OS group, took the stage at its Build developer conference, he joked that he should have come out chanting “Developers, developers, developers.” It was a friendly jibe at the company’s recently departed CEO Steve Ballmer, but it was also revealing look at where the company’s head is at: a formerly all-business organization, known for bullying even, that’s learned from its past and is trying really hard to be everyone’s friend.

It gave a free Xbox One to everyone attending Build, plus a $500 gift card to the Microsoft Store so they can purchase any device. A bribe? Maybe. But I think Microsoft would argue that it’s a friendly gesture from a friendlier company. One where there were no snarky slaps at competitors, where there was confidence without the braggadocio.

Instead, we saw the company’s new CEO, Satya Nadella, onstage answering questions from developers. “What’s the best way for me to have a dialogue with 5,000 of my closest developer friends,” he asked. He leads a Microsoft that’s lost much of the swagger and surety it demonstrated for much of the past 20 years, replaced with a mix of humility and confidence. It was the attitude of someone who has gotten punched hard and bloodied, but is still standing. It’s a good look for the company.

After spending most of its existence focused on corporate needs, with Windows 8 Microsoft swung too hard at user experience—and whiffed. Now it’s clearly attempting to find a middle way between the corporate environments where it made its bones and the personal device era that threatens to turn it into a boneyard.

Microsoft today is the company that, at last, released Office for the iPad, showing it has learned it must now go where customers are, rather than expecting them to come to it. But it also wants to let customers know that when they arrive, once they look behind the pretty features, they’ll find real utility. Today’s Microsoft wants to make IT departments, developers and, (oddly) human beings happy. Instead of forcing everyone to be what it wants them to be, it’s now trying to be all things to all people.

Probably the most interesting thing Microsoft announced today, at least for consumers, was Cortana. This is its new digital personal assistant for Windows Phone 8.1, and it’s a solid example of the middle way balancing act the company is trying to pull off. You could view a voice-controlled feature such as this as table stakes for a mobile operating system, something Redmond had to add to compete with iOS’s Siri and Android’s Google Now.

And Cortana does share many features of both of those systems. She (at the announcement, Microsoft’s Joe Belfiore pointedly referred to the program as a “she”) can take on calendaring tasks and help you find a restaurant. She’s smart enough to recognize that when you say “home,” you mean the particular address where you live.

But Cortana also looks like it’s going for the best of what both Apple and Google have to offer—friendliness and power. Google Now is brutally efficient, able to talk to third party apps and dig into your email and calendar to automatically find upcoming events, like plane flights and meetings, and set reminders. Siri is kind of a lightweight by comparison, but she (again, a she) is friendly and approachable. She’s pleasant to work with. Cortana blends both of these styles. With an API that lets developers hook in their third party apps, the ability to root through your email, and Bing-powered search, Cortana looks to be as task-focused as Google Now. But it’s also friendly. It makes jokes. It has a name. She has a name.

And then there is Windows itself.

Windows is now free for smaller devices: phones and tablets with screen sizes less than 9-inches. The Start menu is back, baby, and better than ever with a mix of traditional view of applications, and those live tiles (that it’s just sure you’re going to love) from the Start Screen. The Windows 8.1 update will boot to the desktop automatically if you’re not on a touchscreen. The Start Screen has a contextual menu that pops up with a right-click. A PC Settings tile is now up in the top hand side by default. Searching for apps shows you where they are on their machines, gets you to the All Apps list when you have a new one, and helps drive you to the Store when appropriate. In short: it’s new, but also more familiar.

Then there are developers. An entire generation of developers has hunkered down on iOS, and Microsoft has to get them back. Today it announced a Universal Windows Apps program that lets developers build apps to run on Windows-powered phones, tablets, PCs and even Xbox—which gets them on televisions. They can design an app to run on all of these environments, with customizations for each. They can even let consumers buy it once and download it on each system. Again, it’s a thoughtful, low-pressure way to get developers onboard. It’s indicative of a company that’s listening to developers, rather than dictating to them.

“You want to build for Windows,” Nadella argued, “because we are coming at this with a challenger’s mindset.” They are, he said, no longer the incumbent.

The things is, Windows 8 already tried to have the best of all worlds. But it did so on its own terms. It sought to force everyone into its big, flat buckets. It bet too heavily on touch, and in doing so made users who weren’t on touch devices feel left behind and forgotten. It felt disjointed, a touch-first environment not just bolted on to, but also concealing the familiar desktop.

Now, Microsoft is positioning itself as the ecosystem where you can be you, no matter what kind of device you enter into it with—tablet, phone, desktop, Xbox. It’s as friendly and confident as a human voice, yet also just as complex. It’s promising to give customers both pleasant human-oriented design, and powerful enterprise features. It’s trying to be all things to all people, a company that can make IT managers happy and also make users BY-ing their OD bring a Microsoft device.